Sissy Anal Training Stories

79,685 results
Orientation
Length
Source
Infinite Scroll

Becoming Marc's Sissy

by grizzley123 on Jun 19, 2018
Transsexuals & Crossdressers

This is a story with themes some may not like. If that is you, read it, don't read it, your call. But if you are going to comment, keep in mind that no one required you to read it, and no one requires you to like the themes. Writing nasty comments only makes you look foolish. For others, I would love to hear your comments. And I hope you enjoy the story....

The Journey Ch. 02

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

(You may want to read The Journey before reading this so you will know the background of Tom/Tonya and Jason. These stories are a combination of real life and fiction. Thanks for sharing your comments.) Tonya was content as she stretched across Jason's lap. She had given Jason a long slow blow job and now Jason was rubbing his sissy slut's smooth ass a...

Trapped and Trained Ch. 02

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by the sight of this brunette in a pink corset and black stocki...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

My Life with Little Sparrow

by DomAlphamann on May 11, 2020
Fetish

I almost never come home early unless it's for a good reason. I have two reasons today; one of those being to keep you on your toes, of course, the other one is to give you news. If you followed the rules, as you should always, you might have heard the car pull up, but just in case you were busy doing anything for your own sake and enjoyment and didn't hear...

On the Hunt Ch. 08

by Lisa2506 on Aug 7, 2019
Exhibitionist & Voyeur

Hi, Madam Lisa here. This is part 8 of my real-life ongoing relationship with my subs. The only thing I have changed are the names. I also do not mention the names of the locations. I sure some of you will be able to figure them out. All I ask is you don't tell. Thank you for reading my story. I hope you will enjoy it as much as I have. All participants are...

The Unsuspecting Candidate Ch. 02

by missvicky53 on Sep 11, 2017
Fetish

Part 2 Helen continues Mike's training, this time in a French Maid's uniform The aftershocks of his climax were still coursing through his body as I teased him. "Did you have a nice cum, sissy?" I cooed at his still bound form. "Do you want me to release you now?" "Yes, please," he replied. "I'd like to get dressed now." "And get dressed you shall," I tea...

Sheila's Training Ch. 01

by CeliaisAliena on Sep 15, 2017
Anal

Not for nothing are "Ghost World" and "The Doom Generation" my favorite films. I was made for a stark black bob long before I ever got one, before I saw those movies and even before I discovered black hair dye. Without it I might have ended up looking something like Lotte Lenya in "From Russia With Love." Goddess bless Manic Panic!! It's more than the hair,...

Brianna Meets Mommy

by Sissy_Sammi_ on Jan 7, 2018
Transsexuals & Crossdressers

*Disclosure, all characters are 18+ years of age Brian had another distracted day of school. Dreading each minute of each class, desperately waiting for the day to end so that he could get home. During his breaks he would text Rick, asking about his wife and what Brianna should wear. Once the final bell rang, Brian ran home as fast as he could. He didn't ca...

The Awakening of a Sissy Pt. 06

by sissyjolie4u on Mar 2, 2020
Transgender & Crossdressers

While still admiring myself in the mirror, I received a text from Mistress, that read: I am so happy to hear that you are embracing and accepting that you are and were always meant to be sissy Jolie. Let me assure you, I will assist you and help you blossom into the ultimate sissy that you are meant to be. In time Joe will be completely stripped away. You ha...